Triethylamine → 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine

HRID 1396577Notes

Reaction equation

HRID 1396577 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=O)=[C:4](Cl)[N:3]=1.CCN(CC)CC.O.[NH2:20][NH2:21]>C1COCC1.O>[Cl:8][C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]2[NH:20][N:21]=[CH:9][C:5]=12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 2655462-Amino-4,6-dichloropyrimidine-5-carboxaldehyde

Product 1

HCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4,6-dichloro-pyrimidine-5-carbaldehyde (5 g, 26.04 mmol) is dissolved in THF (125 ml), Et3N (4.13 ml, 29.6 mmol) is added followed by hydrazine monohydrate (1.19 g, 26.04 mmol) in water (15 ml) and the reaction mixture is stirred at room temperature for 1.5 hours. The organic solvent is removed in vacuo and a further 30 ml of water is added to the reaction mixture. The resulting precipitate is collected by filtration and dried under vacuum to afford the title compound.

Workup

  1. customThe organic solvent is removed in vacuo
  2. additiona further 30 ml of water is added to the reaction mixture
  3. filtrationThe resulting precipitate is collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5bce282ca729496db475a8dde911d352
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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